You Know You Love Me, Gossip Girl
by AHigherOctave
Summary: Welcome to the Upper East Side where the clothes make the girl and Godiva chocolate always come with a side of gossip. Here, nothing stays hidden for long, because I find out everything eventually my pretties...and you know I can't keep a secret. XOXO.
1. Princes and Frogs

_**Hey people!**_

You should know by now that princes and princesses of the Upper East Side aren't frogs that are kissed, we're born into our beauty and riches. From the first yellow cashmere bunnies from **FAO Schwartz** to our first black **TSE** cardigans, we've always been royalty. Just like our parents before us were and our children after us will be until the end of time. Or at least until the end of Manhattan…and we always get our happy endings.

Such is the case with **M **and **O**. She's the illegitimate child of the legendary **S** and a mystery man spotted entering her townhouse 18 years ago, a secret so well kept that even I'm in the dark about it. **M**'s just as striking as her mother with those haunting blue orbs that stop traffic and her effortlessly flawless curls…even if she didn't get the trademark pale blond except in tiny streaks. **M **belongs more on a movie screen than she does strutting along **5thAve**. On the other hand **O**, her knight in shining armor, has no mystery in his regal blood. The son of the infamous Queen **B** and her almost runaway king **N** (You didn't actually expect **B **to let him sail off into the sunset without her long, did you?), he's just as lost and forlorn as his father was back in the day. And inheritance seems to have worked in his favor… he's got his mother's glossy dark strands in his shaggy hair and the little flecks of the infamous **N **shade of green in his chocolate brown eyes, and that perfectly white smile. Just like my mother before me fell for his father, I'm falling for innocent little **O**. And you know with me around he won't stay innocent for long. There are rumors for years that he's offered her his family ring last weekend at brunch, but don't believe it until you hear it here. After all I would never lie to you… Besides, this made-in-heaven couple may have bigger problems then you'd know…

**Who's your daddy, M?**

You've all heard the haters in the Constance hallways giggling about their 'brother/sister' relationship…could **M **really be the **N**'s daughter? Well here's for hoping, but I doubt it. Even if **N **and **S **had tried to have another secret fling, don't you think **B** would have demanded a paternity test by now? Besides…how'd **M **end up brunette if she's the product of the two hottest blonds in Manhattan? My money's on either one-time almost boyfriend **D** or military-reformed **C**, **S**'s bed had never had a waiting list. Then there's the rumor about **A**, **B**'s vegan rockstar of a stepbrother. You know I love a mystery…

**Speaking of that…**

I'd like to break some news about a blond bombshell getting off a train at **Grand Central Station**. No, she's not the reincarnation of **S **herself−one surprise offspring was enough for that girl. Though I can see where the confusion is coming from, with those startling baby blues and those luscious locks…and it's been almost exactly twenty years after **S **stepped off the train from Connecticut and wreaked havoc on the city. Apparently she was arriving from an artist's community in Vermont where people make clothes out of hemp and live off each other. For those of you who haven't figured it out already, she's the surprisingly stunning daughter of tortured artist **D** and still bald **V**. Raised by her oddball aunt, she turned up in Brooklyn for no plausible reason. **L**'s about in for a rude awakening, people don't play nice in the city little girl.

**Sightings**

**S** and **M **at the **Plaza** sipping Cosmos and giggling. **O** walking through **Sheep Meadow** and looking lonely…he always knows where to find me. **J**, **C**'s well-groomed son, at the **Elizabeth Arden Red Door Salon** getting his roots touched up. A well-known music trio, let's call them **J3**, enrolling at **St. Judes Prep**…too bad its boys only. **A **and **A**, **M**'s loyal followers, buying cheap **Louis Vuitton** knock-offs from a street vender. Don't those girls know I see everything? And little **L**walking alone in Williamsburg, an **H&M** coat wrapped tightly around her torso and a pale blue **L.L. Bean** duffel strung over her shoulder…at least she's not shopping at the Gap.

**Well my little royals…**

And all you frogs who are still hoping to turn, I don't know about you but I'm just gonna lean back and wait for people to spill. I'll be the first to know…and you know I can't keep a secret.

You know you love me,

Gossip girl


	2. It's M's Party

AN: So what do you think, too weird? Well, it doesn't really matter. I absolutely love it. It may be my favorite thing, it's deliciously evil and it'll only get worse. I've read all the books, and it'll be just as mind-blowingly inappropriate, overly materialistic, and amazingly juicy. So keep reading, and don't expect anything whether it's Moliver or Loliver or else wise…except that J3 will be the JoBros, that's gonna happen.

_**it's m's party**_

"Miley," A male voice whispered huskily from behind her. She smiled at her Prada clad reflection, and scooted back on her 3-½ inch Manolo Blanhiks to the warm body that was calling her. Tonight would be the night. The night of her 16th birthday extravaganza when she'd finally become a woman, and not just because of the extra candle on her cake… It would be the night she stopped being known for her fatherless birth to Serena van der Woodsen, actress and model extraordinaire. From now on she would be known for her wild, hot−but always classy−escapades all around the city with Oliver Adam Archibald. Naturally they'd christen her bed first, before moving on to his, and the park, the corridors of their school…

"Mmm…I'm so hot," She purred as seductively as possible, muzzling against him with her eyes shut and feeling his hands on her hipbones. She grinned wickedly to herself as she felt her skin burn with his touch, "Help me off with my dress?"

"Gladly," He replied, already tearing off the strap of her one-shouldered purple silk number.

Her eyes flew open at the sound of his voice and she pushed him away, fixing her dress. "Jake!" She shouted, shooting daggers at him. "How did you get in here?"

"You're such a tease," He groaned, sitting on the edge of her dark blue comforter. She kicked him with her sharp heel, and he yelped. "You're mother let me in." He paused, lips curling into a sickeningly slimy smile. "Aren't you happy to see me?"

"No," She stated flatly, looking at herself again in her full length mirror. A minute ago she'd thought of her image as perfectly sultry but also respectable. Now the feeling of Jake's dirty fingers on her shoulder had ruined that. She stepped into her closet, slamming the door and hoping he'd get the messaged.

"I brought you a present," He said, leaning against the smooth oak door.

"The only present I want tonight is from Oliver," She called back, holding a red Chloe dress to her frame. She shook her head, placing it back on the hanger. The satin material would have looked beautiful on her−like most things−but it was cut too far up her tennis-toned thighs to say L-O-V-E. Instead it shouted 'Desperate enough to open the door and let Bass boy in'. She shuddered.

"How very The Notebook of you," He snorted, and she heard him shift over towards her bed again.

"Thank you," She smiled, if only they were in the '20s and Oliver could be taken away by war at any moment so she'd need him to ravish right then because if he didn't who knew if they'd ever have the chance again…

"You do realize you don't have strawberry blond hair? Or a sweet Southern disposition?" He mocked, his hiss-like laugh penetrating quite noisily through the door. "Or that Olliekins was born black-haired and rich?" She opened the door to glare at him, popping off one of her impossible-to-walk-in heels and throwing it at him.

His disgusting little smirk just widened though. "If you wanted to play rough, all you had to do was ask van der Woodsen."

She rolled her eyes, turning back to her closet. "You're ruining my night," She reminded him, contemplating a rather pristine ice blue Hérmes. Too virginal.

He seemed happy with his looks though, admiring his reflection in the clean glass doors of her balcony. "I know I wasn't part of your little novel, Miles, but Archibald won't be exactly what you had written in either." She shot him yet another look, "I'm just saying…you're no exactly Mandy Moore in Chasing Liberty." She threw her other heel at him, missing and casing a loud clatter as it hit the glass. "Hey! I meant it as a good thing, the chick's a prude. Did you know she had to have a butt double for that dip in the river?"

She stood in the door of her closet, leaning against the frame in just a fuzzy red robe. "So what exactly should I be expecting then?" She hissed. One hand poised on her hip, choosing to ignore his last comment about the always classy Mandy Moore.

His eyebrows raised and she held his gaze, eager but collected none-the-less. He walked up to her, standing behind her and resting a hand on each shoulder. "You…" He whispered in her ear. "…should be expecting Sarah Michelle Gellar in Cruel Intentions."

Her navy eyes widened and she elbowed him in the stomach as hard as she could. "Pig!" She gasped, embarrassed that she had expected anything less.

"What?" He laughed as she attempted to push him out of her room.

"That girl was a crack whore, emphasis on whore!" She snapped, thrusting the door from its open position.

He caught it with his foot, still smirking evilly. "And she loses her lover boy to that innocent twit." She assumed he meant Reese Witherspoon, who she admired very much."Not that I'd ever make that mistake," He leered at her once more before slamming the door dramatically for her.

"Pig," She repeated bitterly, trudging slowly back to her closet and feeling unnerved that he'd taken the drama out of her moment.

AN: I know this is very Chuck/Blair of them, in fact that "If you wanted to play rough" thing was almost straight from the show. I haven't really decided where I'm going as far as couples are though. I'll get a little bit of everything in, because between the books and the TV show of GG basically the only couple that hasn't happened is Blair/Dan. And that's just so far. Also, what do you think of me putting Mikayla in here? I think if tweaked her a little she'd make a good Vanessa type. And where do I fit Jackson in? Would you be at all disgusted if I so much as hinted a little Mackson if they're not siblings in this story? Let me know. Also, I know the chapters are short but there are going to be _a lot_ of them. So don't worry about it.


	3. O Just Wants a Drink

AN: For all of you Ollie lovers out there, definitely read this chapter. I know we all want Mitchel to cry on our shoulders, but unfortunately, he's in California and I'm on the East Coast, but if he's ever got a concert nearby…I'm here for him…and Cody…and Nick Jonas. I couldn't help but post this, even though I just did one yesterday. I also have some good news concerning my computer, it will be fixed soon! In the next week, so not long after 30 Kisses will be back up and running. Yay! I've missed it so much, and I've finished it completely as of today! I just have to upload…

o just wants a drink

Despite growing up with the queen of the high society, Blair Waldorf, throwing brunches, charity functions and cocktail parties 24/7 in their living room, Oliver always felt left out at Miley's parties. It wasn't that he was outnumbered by her prissy girlfriends. She always invited his core four, Jake, Todd, Matt, and Lucas. He never ran out of things to say and flopped about like a fish on dry land, in fact Miley practically custom-fitted her conversations so he could just drop in a line now and then and still come out the smartest and most cultured guest of the party, with the exception of her, of course. And she never left him underfed, she'd even buy his favorite Ice Cream Sundae flavored Pop tarts in case he got sick of the usual crap with fancy French name that all tasted the same. It was just, why did he feel so…

His thoughts were interrupted by a pair of breasts pressing into his back. "Hi sailor," This was one of Miley's favorite lines. She must have picked it up in one of her _women's novels_. They were the same romance novels his mother read, Gone with the Wind and Danielle Steele but if he called them that she got all mad and threw things at him, so he hadn't since they were thirteen.

"Hi," He mumbled, biting his lip. Why did she feel like teasing him? Hadn't she done that enough? He had turned around to excuse himself to the bathroom when he saw the dress. Usually Miley was obsessed with classy, old Hollywood dresses that his mother loved and often picked out for his girlfriend during her frequent trips to Barney's and Bendel's. This though, it was a strapless black cocktail dress that was completely unlike anything he'd ever seen her in…it was short, tight, low cut, and made her small B-cups look huge. Naïve little Oliver, haven't you ever heard of padding? "Miley," He breathed, pulling her to him. She beamed up at him. "You look..." He paused. The first word that came to his mind was hot, but that would get him nowhere with her except back in the doghouse. "Beautiful," He mumbled shyly, kissing her forehead tenderly. Her eyes shined, and he knew he was in.

"Come on," She whispered, tugging him gently towards the bedroom. She'd have him now, and whatever she wants, she gets. Sound familiar?


	4. Surprise, Surprise V

**AN:** I love being able to be so evil and not being judged for it. I couldn't wait to write this chapter because I'm sure it'll even out some of the questions that the first three, short and juicy chapters didn't. We also get to see two people I love very much.

**Carmendee:** I know! BN was so epic, and now they're giving all their story lines to CB. Chuck is gay in the books for Christ sakes! No one is a literal translation of any of the older chapters, but no-one is quite themselves either. Thank you for catching that B! Miley will be like her, but they'll be different, as will Chuck/Jake…you'll see. I have made up my mind on Mikayla, and someone else although you won't see either or them or what they're like for another few chapters. The adults will be in here for more than just snippets, but I'm building off the HM fan base so you'll have to be patient. I don't like show-Jenny either, I really only like show-Blair, and I _**despise**_show Vanessa.

**nazgurl92: ** Miley is being…well, yeah. Appearances can be deceiving though. I'm not commenting on the couples, I'm just gonna go where the drama takes me. And no-one is anyone. Well, B, N, S, C, V, and D are themselves actually. The HM crew, they're somewhere in the middle between their show selves and their evil sides magnified about a hundred degrees for the Upper East Side.

**c-melle:** I myself am also a total Lollie fan, they're just…gah. Although this story doesn't have any specific couples, any and everything has the possibility of happening. Except Zac Efron, my muse and I have an agreement that he shall never arise in any of my stories unless it is to murder him. There are people who are related, besides G3, but I'm not telling who. I have finally figured out what to do with Jackson! There's too many J's though…and too many M's…

**Princess Cutie: **Loliver. There it is. Jk. We'll see what happens, you never know. I might just make Lackson happen. Or Moliver. Or Lake…and many more.

_surprise, surprise v_

Vanessa Abrams was sitting on the couch, basically drunk, watching the new Ken Mogul movie and wondering how someone she'd once looked up to so much could have become such a sellout. She had just refilled her glass of cheap red wine, and she was swishing the liquid around, watching it rather than the pathetic excuse for an indie film. The door creaked open and she glanced up, only to drop the glass onto the rug of her Brooklyn loft. It splintered into her foot, forcing her to pry her eyes away from the last person she'd ever expected to see. Well, second to last person…but we'll get to that. Won't we?

"Shit," She hissed, leaning down to squeeze her foot.

"Mom, you know you shouldn't do that it'll just make the blood gush," She heard someone from above sigh. "Hold it up and I'll go into the kitchen and get you a towel to stop the bleeding with." Vanessa glared up, but her daughter was already retreating to the kitchen. Her long blond hair fell in a curtain behind her, reminding her of someone else just like always. It was unfair really, that her daughter who came from a line of dark-haired, dark-eyed people should get the recessive, pretty genes so easily and look so much like _her_. Next to her, her date scooted around uncomfortably on her brown leather couch.

Ooo…looks like someone doesn't want to be her new daddy.

"You have a daughter?" He asked, setting his intact wine glass on the table. She nodded glumly, bending her leg so the bleeding was above her heart just as she'd been instructed. "I…uh…you lied to me."

She glared at him, "You never asked." Her daughter came back into the room, holding a black dishtowel and wrapped it around her foot delicately. This had always been the way it was with them, Vanessa had always been the child out of the two of them.

"Uh, hi," He said to the beautiful teenager standing there, not looking at him. She still failed to acknowledge his existence.

Meow, someone brought their claws with them. She'll need them here.

"You should probably leave," He looked at her, and then glanced at the younger Abrams. "Now," She clarified and he stood up, straightening out his shirt.

"I'll call you, alright?" He questioned hopefully, trying to look her in the eye.

"Great," She replied flatly, her brown orbs fixed on the wall. He let himself out and she turned her attention to her daughter, who had let go of the towel and was sitting on the floor in front of her. She had her nose wrinkled in disgust at the movie playing. She snatched the remote and shut it off quickly. Still the girl sat there, staring at the screen and not speaking.

Wow, she must have really inherited her mom's love of black.

They sat there in silence, and Vanessa let her gaze pour into the back of her head, waiting for her to look up. She didn't. "Lilly," Se hissed suddenly. Her daughter peered back at her, blue eyes looking at her tiredly as if she was some toddler in constant need of entertainment. Aw, does V want a cookie? Too bad, it's nap time. "What are you doing here?"

"I'm living here," She stated, not locking eyes with her. "I'm sick of living with Grandma, Grandpa, Ruby, and Piotr. Piotr is trashy and he smells bad, and he's always painting nude people, _with dogs_." Vanessa smiled in spite of herself, he was weird. Perfect for Ruby maybe, but definitely a nutcase. "And Grandpa hardly ever wears clothes, I'm sick of getting up in the morning to have breakfast only to have it ruined by the fact that I can't concentrate on my Cocoa Puffs because he's making a new sculpture and his butt is on display." That had been a problem in her childhood too, especially when she'd had people over. "You aren't making me leave again. If you do, I'm going to live with Dad. I don't care if you hate him or not. I'm sick of being a freak just because you can't stand the fact that I'm better than you at everything." Here's a case of the apple falling so far from the tree it became a flower in the process.

Vanessa sighed. If she sent her away, she'd keep her word and go live with Dan. And Dan would ruin her. If she stayed here…Mommy would end up jumping out the window? "Get your coat," She grumbled, pushing herself off the floor. Hopefully her Doc Marten's wouldn't be too painful on her freshly scared foot. Lilly shook her head, staying where she was. "We're not leaving, you can stay here. For now, at least."

Lilly marched into the kitchen, coming back with her gray, bubble-material coat. "Where are we going?" She asked, the corners of her mouth turning up in a playful smile. She'd always loved surprises, even the bad ones like her 6th birthday party when grandpa had gotten her an alpaca. Can you saw _ew_?

"The Archibalds," Vanessa returned, swinging open the metal door. Lilly just looked confused.

Looks like someone's feeding her little bunny to the wolves.

**AN: **OMG, they're going to Blair and Nate's? Where little Miss M is? And Jake? What will happen? Why haven't we seen the Jonas Brothers? Is this a Moliver story or a Loliver?

Who knows, but as they say New York never sleeps.


	5. M, Interrupted

**AN:** I realize the ending of the last chapter was a little confusing. As is the rest of the story, since it's unclear to all of you which characters have met and which ones are complete and total strangers.

**1italianbella**: Oliver is Blair and Nate's son. Lilly is Dan and Vanessa's daughter. And Miley is Serena's illegitimate child. The other characters and their offspring will be making an appearance, or maybe several, but I'm gonna wait to tell you those ones. Lilly will meet everyone, or maybe she's already met everyone a long time ago? Guess you'll have to wait and find out…

**Nazgurl92**: No, V hardly knows N because the GG part is more based on the books than the TV show. And you'll see why they're going. And I'll let the Miley/Lilly part explain itself, because it's more fun for me that way.

**c-melle**: I cannot explain my animosity to Zac Efron behind the fact that he's always made me want to twist his arm behind his back, even in his pre-High School Musical days…I'm trying to find a way to clear up the Js and Ms. Like the Jonas bros got changed to the Gray brothers so I don't have to deal with the J from their last name or the J from Joe. If I put Jackson in I'll have to make him have some initial thing like J.K. or something. Same with Mikayla. I dunno, I'll figure it out.

**Carmandee**: We'll see D before long and figure out why he and V are on the outs. B and V…it'll be explained. I _really_ want to tell you but I have to fight myself because I'll ruin too much of the plot. I think we'll definitely get to see B's reaction to her daughter dating a non-Upper East Sider sooner or later, even if it isn't Lilly. And the sailboat thing is very tempting to do…

_m, interrupted_

His shirt was finally off. After struggling for several minutes with the button she'd finally managed to throw it to the floor. And there was nothing better in the world to her than a shirtless Oliver Archibald. Amen to that. She kissed her way down his chest, so eager. She fiddled with the belt of his pants. It was stuck!

She yanked it hard, and then attempted to unclasp it again but it stayed sealed tight. What is this, B's version of a chastity belt or something? He groaned in frustration, and jerked it out of her hands. Within about ten seconds he had it off himself and he was working on her dress. He pulled the zipper but he felt in sang in the middle. He fiddled with it awkwardly, trying to fix the jam. She watched him, smiling, and tilted his chin towards her. "Oliver," She breathed, looking at him.

He turned his head back to her dress. "Uh-huh," He mumbled, shaking the material hard.

"Oliver!" She snapped, but as soon as he looked up at her with those big brown eyes her tone softened. "Oliver…" She whispered, "I love you." He froze, feeling himself get sweatier than in all the time that they'd been trying to just get the hell out of their clothes. Doesn't that tell you something's wrong, O? We know quite a few people who'd be willing to kiss it better.

She'd said this to him a lot since the summer after 9th when they'd gotten together and more often than not it was followed by _but I'm not ready_ which had gotten him out of saying it, because he could blame it on being pissed that she wasn't putting out. What did he do now? If he didn't say it, she would be offended and turned off and would probably kick him out of her bedroom now, possibly without his clothes. If he did though, he'd be…well, not lying…but did he love her? Was this love? Poor little Oliver, just tell the girl what she wants to here.

Meanwhile in the living room, Serena van der Woodsen was sipping coyly at her glass of champagne. She threw her long, blond head back as she laughed at Richard's jokes. Richard Norfolk was the head of advertising at Microsoft, and worth almost as much money as Bill Gates himself. And he was totally smitten with her…of course, it also didn't help that he had short but still wavy jet black hair and twinkling blue eyes she could get lost in. Now if only he would start talking about something other than numbers. Or he could keep doing so and just talk about size rather than dollars…

There was a loud rap on the door, and she rolled her eyes. Why couldn't Miley's friends just get the doorman to buzz them in ahead of time? She made her way to the door, her Jimmy Choos clattering against the wooden floor. She swung the door open and was greeted by the last two people she ever expected to see in her life.

"Vanessa?" She asked incredulously looking at the still bald, but much older version of her high school friend. Then she looked at the person next to her, already a head above her mother. The rumors were true, she did look stunning, very reminiscent of herself in days past from the perfectly messy blond hair to the stunning navy eyes that stopped traffic. Except there was something different about her, Serena just couldn't put her finger on it…

"Is Blair here?" She huffed, she'd just run the two blocks between Blair and Nate's beautiful townhouse and Serena's penthouse. Lilly, however, didn't seem out of breath or stressed in the least. She bit her nail as she stared in inquiringly.

"Uh, no, she and Nate are in France right now. Oliver's here though." She turned around to look for her best friends' son but no luck. So she glanced around for her daughter. No such luck.

"Oliver?" The younger blond asked quizzically. "Who's he?" Just then a boy with shaggy brown hair was shoved into the hallway, he was shirtless. And he was hot…um, cute. She meant cute obviously. She watched as the haughty brunette whipped his shirt at him and he caught it.

"Miley," His soothing voice pleaded. "I just thought, you know, it was a corny time to say it."

"Get out! Get out of my apartment this instant Oliver Adam Archibald!" She pounded her little fists onto him as he backed towards the door while trying to block her. Looks like someone doesn't like it rough…poor boy doesn't know what he's missing.

"Miley!" Serena went red with embarrassment, here was Vanessa's stunning daughter acting all polite and well-behaved like a lady. And hers, well, she was throwing a tantrum like a five-year-old. "He's staying here!" She hissed, stepping between her daughter and the boy being pushed into Vanessa and her daughter.

"I don't care! I want him out!" She screamed, trying to kick him again and succeeding in scaring Serena's leg. "And why is there some bald freak standing at our door?" She looked her up and down before turning to the beautiful girl about her age next to her, who was _way_ underdressed for her dinner party. "Who are _you_?" She snapped.

"Lilly Humphrey," She stated, looking warily at the drama queen in front of her in the slutty dress.

Humphrey, Humphrey, she'd heard that name before…no. She couldn't be.


	6. It's Hard To Live in the City

**Hey people!**

Don't you love the smell of New York in the winter? How the cold air burns your nostrils the way expensive whiskey burns your throat, the way delicate flakes of snow falls onto the ground the way **La Perla** panties fall to your floor, the way you see happy couples keeping each other warm on a bench in **Central Park**…ew.

**The people who are in love who we hate**

Maybe it's just me, but I'm so sick of happy couples. And as of 10 PM we have one less to deal with. You've seen them on park benches all over the city, on the steps of the **Met**, cuddling while looking at the penguins of the **Central Park Zoo**, trying to devour each other's faces on the corner between their two same-sex schools before the first bell, during lunch, before soccer practice…Blech. No longer will we have to watch as she stands tippy toes in her **Kate Spade** flats to reach his lips and clings to his baby blue **Brooks Brothers **button-up shirt. So girls, spring for the new sultry sex-kitten haircut you've been thinking about and treat yourself to the sexiest panties you can find whether they be from the all-new **Stella McCartney** collection or **Victoria Secret's **catalogue because the hottest boy in the city is officially back on the market. Don't spend too long rejoicing though, you never know when the **Manhattan's **stupidest girl will realize what she's done…or when someone else who's had their eye on him for years will decide to jump his bones rather than waste time being subtle. After all, I'm your competition, grr.

**Our favorite trio to hold concert…**

By now I'm sure you all know that our favorite trio, a certain **G3** has arrived to spend some time working on their new album on the East Coast circuit. And I'm sure a lot of you obsessive fan girls out there are already camped out in their apartment in the snow waiting to try and touch them when they walk out to school. Why though? My sources tell me that they're holding a charity concert at a certain **St. Judes School for Boys**. If you aren't a certain beautiful brunette hunk with mesmerizing chocolate colored eyes…or even a hunk that may be blond and gorgeous but way too aware of it don't worry, it's also open to **Constance Billard** and **Riverside Prep **students…and, gag, **L'Ecole**, um,sophisticated young ladies…right. So double the request for new fancy panties because you'll need them to throw onstage, or for sneaking backstage after the show. Sometimes it's fun to be a groupie…

**Q & A**

**Q:** Dear Gossip Girl,  
Are all girls in the city psycho or just the girls I know? Is there any way to tell or is it all just luck? Are you sane? Are you as hot as you lead on? Who are you?  
-BeingStalkedByCrazies

**A: **Dear BSBC,  
Sadly all of us get crazy sometimes. If you're lucky you'll find someone who's crazy in bed, if not, well, I apologize. I dunno if I'm your definition of sane or not…but either way. I'm worth it. And good luck finding out who I am. It's like **Carly Simon** says about who **You're So Vain **is written about: "Those who think they know…don't."  
Love, GG

**Q: **Dear GG,  
I heard that **L **and **M **went to tennis camp together years ago on Cape Cod. They had they're own cabin and totally spent the whole time having sex. Is it true? Is **M **a total lesbo? Is that why she's the only one in the state who doesn't jump at the thought of screwing **O**?  
-LonelyGirl

**A: **Dear LG,  
While I can definitely confirm that **M **spends her summers playing tennis on Nantucket, I can also confirm that **L **has never been there. And as to why she hasn't slept with **O**, even I'm not sure. I mean you've seen the boy, right?  
-GG  
P.S. They're=They are. Their is the possessive you wanted to use.

**Sightings**

**O **being kicked out of **M**'s penthouse and checking into a suite at his mother's Alma matter, the **Yale Club**. **V **returning to Williamsburg minus little **L**. Has **M **found someone she's willing to play nice with for once? **S **on the balcony of her apartment in a terrycloth robe from **Barney's** puffing away on a **Merit Light**. **J** stumbling drunkenly into a cab with **M**'s besties **A **and **A**. Well, if he can't get the real deal he might as well take an imposter. **N**'s yacht pulling into **Battery Park** with both him and **B **looking under bathed and over sexed. Looks like some people had fun in the country of romance.

Well my pretties, I've got more people to watch so I can tell. I hate not sharing good news…and all news is good news, right?

You know you love me,

Gossip girl

**AN: **I am so tempted to put up a second chapter today because I have it done and its…gah. Can't though. It sucks. I'm not patient, never have been, never will be.


	7. OMG, It's Connect Three

**AN: **I do not think Camp Rock is a crappy movie. I love it and I'm a Smitchie/Jemi fan. And it is not the movie that Lilly is referring to, for the purposes of this story they have an ABC Family movie where they all meet the same girl at different times and fall in love with her, and then Shane (Joe) gets her, predictably enough. The girl is played by Vanessa Hudgens. Jason (Kevin) ends up with Mandy Moore's character (a random, semi-nerdy girl who wants to backpack across Europe). Nate (Nick) drowns in a river saving Shane's life. Not in this GG story, in the TV movie. I don't know why he does in the movie either. Basically does because it just struck me.

_omg, it's connect three_

"I love you, Nathan Samuel Grey!" She heard a voice shout as she walked into the school with Miley, tottering on her impossibly high strappy sandals. She was grateful that she'd been taken under her wing. But did she really have to throw her head first into the world of high class Manhattan fashion?

Yes, because really, having designer clothes totaling thousands of dollars thrown at you is such drag.

Miley wrinkled her nose and linked her arm in her new friend's. "God, some of these trashy L'Ecole girls really have no taste. I swear to god, they just throw themselves at the first thing that moves!" Whereas she just throws herself at the first guy she sees, literally.

"I don't really see what's so great about them." Lilly shrugged, and the strapless ice blue dress Miley had chosen for her slipped down a little bit yet again. She tried to tug it up subtly, Miley's deep purple dress was spaghetti strapped and therefore, she didn't have the same problem. "I mean, yeah they're hot." _Oliver is hotter_, she thought glancing around the courtyard for him. She'd been hoping to see him ever since her first night in New York, as Miley had gotten rid of him once and for all they'd locked eyes. And something inside her had clicked, taking her breath away. "But plenty of guys are hot, and they have more to offer than songs that are overplayed on the radio and crappy TV movies." Like Oliver has a wing in his very own townhouse and a whole bunch of pretty boats?

"I know, before they were big I totally had a thing for Nate, but then they totally sold out and I got _so _sick of Amber and Ashley talking about them. I mean, like they'd _ever _notice those two." Miley nodded eagerly, she loved her new friend. She was so pretty, and sweet, and totally new and fresh. Translation: She was amazed by everything Miley did, and complimented her mercilessly.

Lilly snorted, watching as Ashley Farkas and Amber Coates stood in front of the stage waiting for the three brothers to come on and omitting squeals every few minutes. "Especially with those matching outfits, do they seriously think that's cool after fourth grade?" She and Miley snickered as they studied their ugly matching orange and royal blue dresses. It was like they had raided some bad vintage costume place down in Brooklyn. Maybe they thought it counted as vintage?

"I'm gonna go grab some drinks," Miley told her, grinning. "Want anything?"

"Um," Lilly mumbled, biting her pointer nail nervously. She wasn't used to drinking much other than the wine that her grandparent's neighbors, the Butterworths, made themselves which was really was glorified grape juice. She'd learned over the last few days that while she was basically an alcohol virgin, Miley was not. She drank champagne with brunch, and wine with dinner. And then she'd mix cocktails afterwards that they would sip while watching movies like _Sleepless in Seattle _and _Titanic_. Luckily before now, Miley had just given her whatever she was having so she hadn't needed to lie about the fact that she never drank. "I kind of feel like an appletini, do you guys drink those?" It was one of the few drinks she knew the name of besides scotch on the rocks with a twist and screwdriver. Scotch on the rocks sounded like something an old man with ear fungus or something would drink, and screwdriver sounded like a slut drink, not to mention it was half made of juice. So she'd used the drink she'd learned of from J.D. on Scrubs.

"Ohmigod, that sounds so great right now," Miley smiled, slinging her arm over her new BFF's shoulder and giving it a squeeze. "Be back in a sec," She felt light and effortlessly happy as she breezed through the hoards of C3 fans towards the bar. When she kicked Oliver out of her bedroom for not saying those three little words, in her mind she'd thought she'd be miserable until he apologized. She thought that she'd cry herself to sleep every night and become one of those pathetic girls who waits and waits for another chance at a relationship that had clearly expired. Seeing Lilly at the door had changed everything.

She had obviously needed a place to stay, and hearing the name Humphrey, a short-lived fling from her mother's senior year of high school had immediately sparked a love for the girl in her heart. So she'd offered to the weird, bald woman she could hardly believe was Lilly's mother that she could stay in the guest room until they figured out a more permanent situation for her. And to her own beautiful mother's obvious dismay, she'd accepted and left Lilly there.

That first night they hadn't slept a wink. They'd stayed up all night exchanging stories from their very different lives, and watching movies she loved. And the weird thing was, despite being raised by such freakish people (Lilly's words, not hers), they got along so well. She totally understood the romantic movies Miley worshipped, and despite being an obvious newbie to the fashion scene, she had impeccable taste. She hadn't even thought about the break-up.

What she was thinking about was the bar line being way too long. It was full of slutty girls from the aforementioned French school who had bad platinum blond dye-jobs and even worse fake nails that were trying to get drunk off cheap vodka and would hook up with whatever guy claimed to know the band when the real deal had gotten their pick. Suddenly they disgusted her so much she cracked open a door to the school just to get away from them. In the back of her mind, she knew one of them would end up with Oliver, _her Oliver_, before the night was over. She slid down on the bottom of a nearby staircase to the second floor. Out of the blue, she felt weirdly dizzy she didn't think she could stand up.

Maybe somebody hasn't moved on as far in three days as she thought she had.

"Oh god," She heard a voice behind her. And she fought to hold back the sniffles threatening to erupt from her.

"Can't you see I'm-" She turned around to snap at whoever the offender was so she could cry in peace when she saw a familiar face. Well, it wasn't like she'd actually ever seen him before actually, not really. She'd seen that bushy head of his on TV, on the covers of magazines, and plastered on just about every wall of her friends' bedrooms though. Her eyes widened and she looked down, "Oh."

"I'm sorry," He muttered, sitting down next to her. "I thought you were a stalker or something." He pulled out a handkerchief and offered it to her. She took it, smiling through her watery eyes. How gentlemanly, no-one carried around handkerchiefs anymore. Wouldn't it be nice to have a boyfriend who would always dry your tears for you?

Looks like someone's found her knight in shining armor…but don't get too ahead of yourself there, M. Aren't you forgetting someone? Someone you were just going to cry over?

She dabbed her eyes quickly, dropping the navy blue silk square in her lap, "It's alright. I just go so emotional, thinking about the kids who this concert would help. I volunteered at St. Judes last summer," St. Judes was in the city, right? "And I know the kids would just love to know that something like this was all going on for them." An excuse for underage kids to get drunk and sleep around just for them, I'm sure they're hearts would be filled with joy.

"Wow, you'll have to write to them." He smiled at her admiringly. Poor naïve little boy, clearly no-one warned him.

"I will," She beamed back at him. She held out her hand, "I'm Miley."

"Nate," He took her hand, not shaking in but holding it delicately. "If you have some time, we're hanging out for a while upstairs. You could meet my brother and his girlfriend, and my other brother if he ever gets out of wardrobe."

She laughed carefully, making sure her voice would tinkle sweetly so he'd be even more amazed by her. "I'd love to, but I'm supposed to be getting some ginger ale for my friend. She felt kind of sick."

"Why don't you bring her then?" He offered generously. "I'm sure we have some saltines somewhere and they'd be a lot better for her than this caviar and brie crap that's all around here."

She smiled tightly at him. Did he really think they served caviar and brie at events like these? How utterly repulsive, they served oysters and pâté and Crème Brule. "I'll go get her." Still he was so cute, and a pop star.

And therefore by extension, he was filthy rich.

"I'll be waiting," He waved as she pushed open the heavy wooden door. She walked towards the crowd but couldn't spot Lilly anywhere. Why had she let her friend wear the baby heels? She scanned the crowd again, and then turned back around agitatedly…maybe Lilly had gone to look for her at the bar. Instead of seeing the blond beauty, she came face-to-face with Oliver.

She scowled, "What do you want, Archibald?" She hissed at him, he looked so sad and forlorn in his carefully pressed Armani tux. It was navy blue and it made his dark eyes seem even darker and more inviting. She tried to ignore this though.

"I just wanted to apologize again for the other night, I was so stupid…I should have never-" He sounded sincerely, genuinely sorry. She had to stop it.

"Sure, whatever, no problem, we were never great together anyways," She interrupted, peering impatiently around him to look for Lilly.

"Seriously, I want to make this up to you Miley," He tried to take her hand in his but she snatched it away like he had burned it. He felt his frown deepen. He thought she'd be desperate to forgive him by now, what had changed?

Maybe she found someone hotter. Yeah, right.

"There's nothing to make up, Oliver," She sighed, patting him coldly on the shoulder. "I forgive you…I just don't think we should get back together."

"There must be something I can do-" He persisted, his forehead crinkling in thought.

"You want to do something for me?" She barked at him, causing him to jump ever so slightly. "Go find the blond girl who was in the doorway of my apartment the night of my birthday when you left. Bring her an appletini, and entertain her until the concerts over, than bring her to my house afterwards, okay?" She asked, crossing her arms over her chest.

He attempted to look into her eyes but she looked down. Slowly he nodded, "Okay Miles, if that's what you really want," He whispered sadly.

"It is," She insisted, turning her back on him and clomping towards the door. She stopped midway and looked back to see him standing there, "Her name is Lilly."

"Lilly," He repeated as Miley stomped off, and suddenly a stunning blond girl leaning against the wall in the corner turned to stare at him. He felt his eyes widen. What was Miley trying to do to him?

**AN:** I know I'm horrible leaving you with a cliffhanger like this and I'm sorry but this chapter was too long for GG standards. I'm also sorry that I didn't get the two people besides the Grey brothers that I promised but they will be included in the next chapter. They were supposed to be in this one but I didn't expect Miley to take so long with her part. So give me suggestions for sudden mysterious visitors to bring into the fabulous lives of Manhattan's elite. If you could give me an excuse for David Henrie to be there, I'd love you forever. I just love to think about him because he's so drool worthy. Although he can't be Justin, I have too many Js already.

I'd also like to shamelessly advertise for my two Christmas fics, _All She Wants For Christmas_ and _Really, Really_. One is kind of angsty and different. And maybe a little confusing. The other, a fluffy little two-shot. You'll see if you go read them...lol, I'm such a post whore. Love you guys.


	8. Quit Playing Games With O's Heart

_quit playing games with o's heart_

It would have made perfect sense if Miley'd set him up with an ugly girl. She would have obviously wanted to suffer, and he'd have spent the evening entertaining said girl. He would have walked her back to her apartment and given her a kiss on the cheek at the door that would have made her lifetime and Miley would be happy…probably enough to forgive him.

There were no rules for hanging out with a pretty girl, even on the level of Amber or Ashley. She was clearly not in the same category, with her shimmery blue dress that made her eyes seem so dazzling he was struggling to remember what his ex looked liked. And he hadn't even talked to her yet.

It okay, O, we all know you have better things to do with your time than talk.

He smiled tentatively at the stunning girl in question. "I'm Oliver," He offered his hand, awkwardly pulling it from his pants pocket.

She laughed at his hand poised midair, but took it anyways, "Lilly." He blushed. "What?" She chuckled lightly and he turned an even deeper red.

"Uh, nothing," He mumbled, shoving his hand back into his pockets. It's just he wasn't exactly used to being laughed at. Gawked at, yes. Never had anyone ever laughed at him though. "Are you new around here?"

She nodded, her pretty pink lips stretching into a grin, "Um, kind of," A piece of her hair fell, hitting the light from the stage and shining so violently he had to dig his nails into his hand to keep from sweeping it back for her. Yeah, he definitely hadn't seen her before.

Right…because keeping track of girls has always been strong suit.

"I'm from Vermont, but I've spent a lot of time in Brooklyn in the summers with my mom."

"Brooklyn, I…" She looked right into his eyes, startling him so much he lost his train of thought. "I…I've never been there." He gulped, he wasn't used to honesty. When he did end up using it Miley usually ended up being abusive. Or his mother cried and threw things. So he tended to just shut up.

She surprised him though. A quiet grin spread slowly onto her lips. "Yeah, you didn't strike me as the type to spend time there."

He smiled shyly at her, "What? You think I'm just some spoiled rich boy?" She laughed at him again and he jumped a little.

"Well, let's just say that in Williamsburg guys don't usually wear tuxes like that unless they want to be beaten," She grinned. "And they aren't usually intimidated by someone as short as me."

Despite his best efforts to hold it in, he chuckled, "First of all, you don't look so short with the heels of death on. Second, you're friends with Miley, aren't you? Doesn't that prove that things that come in small packages are worthy of fearing?"

"Aw yes," She nodded, then flashing him her cocky smile again, added, "I caught the shoe throwing show the other night, definitely not suitable for children." She looked up at the stage, seeing some teacher or another from the school drawling on about the charity they were there to support. "Do you guys do things like this a lot?"

"Go to concerts?" He shrugged, watching her nervously. She was friends with Miley. She had to have talons, right? "Sometimes, not as much since we hit puberty and Miley got over her Britney Spears obsession."

She rolled her eyes, looking back over at him, "I meant these events and stuff. Is this like your life, going to fundraisers or auctions and benefits?"

He looked down and shifted uneasily. She had talons alright, and in the worst way, she hurt you when she was _trying _to be nice. He did that a lot too though, could her really blame her? "No, we do other stuff."

"Like what?" She asked, her navy eyes staring up at him inquisitively.

"We, uh," He stuttered. "We get drunk in Jake's suites at various hotels and take pictures half-naked in the hot tub. We take our parents' boats out for the weekend to have sex and get stoned off our asses. And the girls, they shop a lot and get their hair done."

"Who do you screw while they do that?" She asked, not seemingly repulsed at all by all the horrible information he'd just given her.

He shrugged again, "Other girls, sometimes we're tired and we just lay around in Sheep Meadow, smoke more."

She sighed, "I've never smoked pot in my life. My grandpa's the only one I know who does and he tends to take off his clothes under the influence of any drugs."

He laughed heartily for a minute. And then they were silent, after about ten seconds had passed he cleared his throat. "So what _do_ you do for fun?" He asked.

She smirked, "Do you really like Connect Three?" She asked him and his face went blank. Why was she avoiding his question?

Maybe Cinderella's worried about turning back into a pumpkin before the stroke of midnight.

"Am I an overly hormonal teenage girl?" He grinned back. Two could play that game.

"I hope not," She teased, taking his hand and pulling him through the crowd.

"Me too," He retorted, letting her. "Where are we going?" He inquired as they neared the gates of the courtyard.

"You asked what I liked to do," She raised an eyebrow at him and suddenly they were on the streets again, with sounds of cabs passing and an ambulance siren faint in the background. She stood on the curb in all of her made over glory.

What's the matter, O? Are you afraid of playing your own games?

**AN: **I know, long time since I've updated and _another_ cliff hanger. The next chapter will be up soon and it's centric to two or three characters you haven't been introduced to yet. As well, I have a new story called _Falling Unconsciously_, it's very philosophical and angsty. I'm loving writing it. There's also a new one-shot of mine up called _You've Got Mail_, it's Loliver fluff with some Jiley and some Moliver friendship. And look out for two new one-shots soon to come _Jake Ryan: American Hero_ and _Never Wanted_ which are Jake and Lilly centric, respectively. Also two full0fledged stories soon to come, _Once Upon a Dream _(slightly based on the Emily Osment song) and an untitled Miley-centric angst/romance as well as the much anticipated second-half of _30 Kisses_. As if all that isn't enough I've started a new Livejournal community for my writing under ahigheroctave. The link will be in my profile soon if it isn't already. It has the dresses I've included so far in the story in the first entry. Love you guys, thanks for taking the time to read this most massive of author's notes.


	9. Don't Forget

**AN:** So I was planning on posting this…uh, never. Well, not literally, because I'm not that hateful. I just wasn't making it my first priority. I got a fairly rude review first thing in my inbox when I came home from vacation. Then I received such a nice one I couldn't help but write. So you can all thank blueSKIES247 for this update, 'cause she's awesome.

_**don't forget**_

"Jackson, get your ass over here!" A black haired seemingly, Hispanic girl waved at him, practically standing on top of her seat.

He pushed his way through the crowd and smiled at her, "Jesus Christ, Mikayla, keep it in your pants, will you?"

She snorted at him, pushing a curl behind her ear. "I'll try," She sniped sarcastically.

"You know you want me," He quipped back, with a little smirk.

"Only in your dreams," She rolled her eyes, looking towards the stage. He stood there, admiring her profile. Her brown eyes, her full lips, her shimmery skin.

In his dreams, indeed.

"Who's playing tonight?" He asked loudly, over the crowd. The Five and Dime was usually empty besides the two of them and Cooper, the bartender. It was one of the reasons they got away with drinking underage, because no-one was ever there to see them.

"I don't know," She mumbled, pressing her beer to her lips. "From what I gather from Cooper quote 'some hot girl'."

Jackson cracked a smile at his friend, who was currently fixing a drink for a heavily tattooed woman in a halter top. That sounded like him alright. "How helpful," He raised his eyebrows.

"I know, right?" She laughed, and he felt his heart speed up. Damn it, he cursed himself. It's not like he meant to fall in love with his best friend. It had just sort of…happened. Just like he'd _happened_. The son of Aaron Rose and Jenny Humphrey, the most unlikely combination in the book. And if his parents were proof odd pairs worked, why couldn't he and Mikayla?

"Hey, Mickey," He started.

"Ssh," She mumbled, holding a hand to him, and staring at the brunette girl walking on to stage. "It's starting."

"Yeah," He mumbled, looking down into his drink.

"Ladies and gentleman, please welcome Miss Mitchie Torres!" The crowd applauded and the pale girl on stage smiled. She had a huge, almost obnoxiously big smile. Or so Jackson thought.

"Hi," She said excitedly. "This song is called…well, um, I guess I'll play it first and then tell you." She went to grab the microphone but accidentally knocked over the stand instead. "Oops…one second." She picked it up, blushing bright red.

Looks like someone's new to showbiz.

She opened her mouth, and then it came,

"_Did you forget,_

_That I was even alive?_

_Did you forget,_

_Everything we ever had?_

_Did you forget?_

_Did you forget…_

_About me?_"

**AN: **I know it's short but it's a little bit of a filler chapter to get to more of the good stuff. And to introduce the Brooklyn scene.


End file.
